P-Toluenesulfonylhydrazide → 1-Cyano-1-phenyl-2-ethylcyclopropane

HRID 434614

Reaktionsgleichung

Reaktionsgleichung von HRID 434614
C(C1CC1)=C.S(NN)(C1C=CC(C)=CC=1)(=O)=O.[C:18]([C:20]1([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:22][CH:21]1[CH:23]=[CH2:24])#[N:19]>COCCOCCOC>[C:18]([C:20]1([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH2:22][CH:21]1[CH2:23][CH3:24])#[N:19]

Komponenten

5

Edukt 3

HCID 15303P-Toluenesulfonylhydrazide2×HCID 136498EthenylcyclopropaneHCID 150627211-Cyano-1-phenyl-2-vinylcyclopropane

Produkt 1

HCID 204915811-Cyano-1-phenyl-2-ethylcyclopropaneAusbeute 51 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8150DiglymeLösungsmittel

Versuchsvorschrift

1-Cyano-1-phenyl-2-ethylcyclopropane was prepared by carrying out a reduction on the corresponding 2-vinylcyclopropane derivative, prepared in accordance with the procedure of Example I, employing tosyl hydrazine. The 1-cyano-1-phenyl-2-vinylcyclopropane (10.14 g) was combined with 22.32 g tosyl hydrazine in 70 cc diglyme and the mixture refluxed with stirring for 1 hour. The reaction mixture was extracted with petroleum ether and, upon distillation, 5.23 g 1-cyano-1-phenyl-2-ethylcyclopropane was obtained. Reduction of the vinyl group was confirmed by the nuclear magnetic resonance spectrum in that there was no absorption at δ5.3. Absence of vinyl absorption was also confirmed by infrared analysis.

Aufarbeitung

  1. custom1-Cyano-1-phenyl-2-ethylcyclopropane was prepared
  2. customprepared in accordance with the procedure of Example I
  3. temperaturethe mixture refluxed
  4. extractionThe reaction mixture was extracted with petroleum ether and, upon distillation

Quellen und Nachweise

ORD-Eintrag
ord-eb81ec22926446758f9aaa6be41039eb
Quelldatensatz
uspto-grants-1983_08
Patentnummer
US04399076

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